idk if this is a programming specific question. It feels more like “perfectionism” or a low-level OCD. For the programming piece, using some sort of task tracking system might be helpful. For example, after a task has been completed (aka a solution was found), move on to the next predefined task.

Another vaguely related term: premature optimization

To add, here’s an example of my OpenVPN config addition to ensure 192.168.3.* is accessible over VPN

verb 5
push "route 192.168.3.0 255.255.255.0 vpn_gateway"

imo, this situation is way too complex for internet strangers to effectively help with. It’s definitely worthwhile to seek out therapy to help process these feelings and to make a plan for resolving some of the deeper issues at play.